Antifungal Effect of Amentoflavone derived from Selaginella tamariscina

  • Jung, Hyun-Jun (Department of Microbiology, College of Natural Sciences, Kyungpook National University) ;
  • Sung, Woo-Sang (Department of Microbiology, College of Natural Sciences, Kyungpook National University,Agro-Biotechnology Education Center, Kyungpook National University) ;
  • Yeo, Soo-Hwan (The Center for Traditional Microorganism Resources (TMR), Keimyung University) ;
  • Kim, Hyun-Soo (The Center for Traditional Microorganism Resources (TMR), Keimyung University) ;
  • Lee, In-Seon (The Center for Traditional Microorganism Resources (TMR), Keimyung University) ;
  • Woo, Eun-Rhan (College of Pharmacy, Chosun University) ;
  • Lee, Dong-Gun (Department of Microbiology, College of Natural Sciences, Kyungpook National University)
  • 발행 : 2006.09.01

초록

Amentoflavone is a plant biflavonoid that was isolated from an ethyl acetate extract of the whole plant of Selaginella tamariscina (Beauv.) spring. 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC were used to determine its structure. Amentoflavone exhibited potent antifungal activity against several pathogenic fungal strains but had a very low hemolytic effect on human erythrocytes. In particular, amentoflavone induced the accumulation of intracellular trehalose on C. albicans as a stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae during pathogenesis. In conclusion, amentoflavone has great potential to be a lead compound for the development of antifungal agents.

키워드

참고문헌

  1. Attfield, P. V., Trehalose accumulates in Saccharomyces cerevisiae during exposure to agents that induce heat shock response. FEBS Lett., 225, 259-263 (1987) https://doi.org/10.1016/0014-5793(87)81170-5
  2. Baureithel, K. H., Buter, K. B., Engesser, A., Burkard, W., and Schaffner, W., Inhibition of benzodiazepine binding in vitro by amentoflavone, a constituent of various species of Hypericum. Pharm. Acta Helvetica, 72, 153-157 (1997) https://doi.org/10.1016/S0031-6865(97)00002-2
  3. Benaroudj, N., Lee, D. H., and Goldberg, A. L., Trehalose accumulation during cellular stress protects cells and cellular proteins from damage by oxygen radicals. J. Biol. Chem., 276, 24261-24267 (1987) https://doi.org/10.1074/jbc.M101487200
  4. Calerone, R. A. and Fonzi, W. A., Virulence factors of Candida albicans. Trends Microbiol., 9, 327-335 (2001) https://doi.org/10.1016/S0966-842X(01)02094-7
  5. Carlo, G. D., Masclo, N., Izzo, A. A., and Capasso, F., Flavonoids: Old and new aspects of a class of natural therapeutic drugs. Life Sci., 65, 337-353 (1999) https://doi.org/10.1016/S0024-3205(99)00120-4
  6. Elbein, A. D., Pan, Y. T., Oastuszak, I., and Carroll, D., New insights on trehalose: a multifunctional molecule. Glycobiology, 13, 17-27 (2003) https://doi.org/10.1093/glycob/cwg047
  7. Gambhir, S. S., Geol, R. K., and Das Gupta, G., Antiinflammatory & anti-ulcerogeinc activity of amentoflavone. Indian J. Med. Res., 85, 689–693 (1987)
  8. Gil, B., Sanz, M. J., Terencio, M. C., Gunasegaran, R., Paya, M., and Alcaraz, M. J., Morelloflavone, a novel biflavonoid inhibitor of human secretory phospholipase A2 with antiinflammatory activity. Biochem. Pharmacol., 53, 733-740 (1997) https://doi.org/10.1016/S0006-2952(96)00773-3
  9. Kim, H. K., Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Amentoflavone, a plant biflavone: a new potential antiinflammatory agent. Arch. Pharm. Res., 21, 406–410 (1998) https://doi.org/10.1007/BF02974634
  10. Kim, H. P., Mani, I., Iversen, L., and Ziboh, V. A., Effects of naturally-occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase form guinea-pigs. Prostaglandins Leukot. Essent. Fatty Acids., 58, 17-24 (1998) https://doi.org/10.1016/S0952-3278(98)90125-9
  11. Krauze-Baranowska, M., Cisowski, W., Wiwart, M., and Madziar, B., Antifungal biflavones from Cupressocyparis leylandii. Planta Med., 65, 572-573 (1999) https://doi.org/10.1055/s-2006-960828
  12. Krauze-Baranowska, M. and Wiwart, M., Antifungal activity of biflavones from Taxus baccata and Ginkgo biloba. Z Naturforsch [C]., 58, 65-69 (2003)
  13. Lee, D. G., Hahm, K.-S., and Shin, S. Y., Structure and fungicidal activity of a synthetic antimicrobial peptide, P8, and its truncated peptides. Biotech. Lett., 26, 337-341 (2004) https://doi.org/10.1023/B:BILE.0000015472.09542.6d
  14. Lee, D. G., Park, Y., Keon, P. I., Jeong, H. G., Woo, E.-R., and Hanm, K.-S., Influence on the plasma membrane of Candida albicans by HP(2-9)-magainin 2(1-2) hybrid peptide. Biochem. Biophys. Res. Commun. 297, 885-889 (2002) https://doi.org/10.1016/S0006-291X(02)02267-2
  15. Lee, H. S., Oh, W. K., Kim, B. Y., Ahn, S. C., Kang, D. O., Shin, D. I., Kim, J., Mheen, T. I., and Ahn, J. S., Inhibition of phospholipase C gamma 1 activity by amentoflavone isolated from Selaginella tamariscina. Planta Med., 62, 293- 296 (1996) https://doi.org/10.1055/s-2006-957887
  16. Lin, L., Kuo, U., and Chou, C., Cytotoxic Biflavonoids from Selaginella delicatula. J. Nat. Prod., 63, 627-630 (2000) https://doi.org/10.1021/np990538m
  17. Lin, Y. M., Flavin, M. T., Schure, R., Chen, F. C., Sidwell, R., Barnard, D. L., Huffman, J. H., and Kern, E. R., Antiviral activities of biflavonoids. Planta med., 65, 120-125 (1999) https://doi.org/10.1055/s-1999-13971
  18. Lobstein-Guth, A., Briancon-Scheid, F., Victoire, C., Haag- Berrurier, M., and Anton, R., Isolation of amentoflavone from Ginkgo biloba. Planta Med., 54, 555-556 (1998)
  19. Ma, S. C., But, P. P., Ooi, V. E., He, Y. H., Lee, S. H., Lee, S. F., and Lin, R. C., Antiviral amentoflavone from Selaginella sinensis, Biol. Pharm. Bull., 24, 311-312 (2001) https://doi.org/10.1248/bpb.24.311
  20. Markham, K. R., Sheppard, C., and Geiger, H., 13C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry, 26, 3335-3337 (1987) https://doi.org/10.1016/S0031-9422(00)82499-1
  21. Matsuoka, S. and Murata, M., Cholesterol markedly reduces ion permeability induced by membrane-bound amphotericin B. Biochim. Biophys. Acta., 1564, 429-434 (2002) https://doi.org/10.1016/S0005-2736(02)00491-1
  22. Mclain, N., Ascanio, R., Baker, C., Strohaver, R. A., and Dolan, J. W., Undeclenic acid inhibits morphogenesis of Candida albicans. Antimicrob. Agents Chemother., 44, 2873-2875 (2000) https://doi.org/10.1128/AAC.44.10.2873-2875.2000
  23. Paik, S. K., Yun, H. S., Sohn, H., and Jin, I., Effect of trehalose accumulation on the intrinsic and acquired thermotolerance on a natural isolate Saccharomyces cerevisiae KNU5377. J. Microbiol. Biotechnol., 13, 85-89 (2003)
  24. Schulze, U., Larsen, M. E., and Villadsen, J., Determination of intracellular trehalose and glycogen in Saccharomyces cerevisiae. Anal. Biochem., 228, 143-149 (1995) https://doi.org/10.1006/abio.1995.1325
  25. Sengupta, S., Jana, M. L., Sengupta, D., and Naskar, A. K., A note on the estimation of microbial glycosidase activities by dinitrosalicylic acid reagent. Appl. Microbiol. Biotech., 53, 732-735 (2000) https://doi.org/10.1007/s002530000327
  26. Shin, S. Y., Kang, S., Lee, D. G., Eom S. H., Song, W. K., and Kim, J. I., CRAMP analogues having potent antibiotic activity against bacterial, fungal, and tumor cells without hemolytic activity. Biochem. Biophys. Res. Commun., 275, 904-909 (2000) https://doi.org/10.1006/bbrc.2000.3269
  27. Silva, G. L., Chai, H., Gupta, M. P., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Beecher, C. W., and Kinghorn, A. D., Cytotoxic biflavonoids from Selaginella willdenowii. Phytochemistry, 40, 129–134 (1995) https://doi.org/10.1016/0031-9422(95)00212-P
  28. Woo, E.-R., Lee, J. Y., Cho, I. J., Kim, S. G., and Kang, K. W., Amentoflavone inhibits the induction of nitric oxide synthase by inhibiting NF-kappaB activation in macrophages. Pharmacol. Res., 51, 539-546 (2005) https://doi.org/10.1016/j.phrs.2005.02.002